Synthetic lubricant



Patented y i 94 UNITED STATES A 2,424,956 PATENT OFFICE 2,424,956 v p pSYNTHETIC LIiBRIcAN'r Orland M. Woodbury, Howard D. Hartough,Pitman,-a'nd Harry J. Alidress; J12, Woodbury, N. J., assignorsto'Socony-Vacuum Oil'Company, Incorporated, a corporation or New York NoDrawing. Attract-tita 944,

This invention has to do With the art of lubrl-' cation and, moreparticularly; has to do with the preparation of synthetic lubricants.-

In the lubricant art considerable progress has been realized in recentyearsin the production of 5 lubricants characterized by one or morespecific properties and adapted for particular usesflln'the main, thisprogress can be attributed-t0 two "dB-I velopments: the first, newrefining procedures and, the second, additionagents capableofz-imparting particularproperties to available lubricants. Althoughthese lubricantsare' somewhat superior to those formerly available inthe art, in general, they too suffer in one or more respects.

For example, while such oils may have superior viscositycharacteristics, etc., they mayhave undesirable oxidationcharacteristics, etc. Recently, however, in an iiort to obtain superiorlubricants endowed with specific and superior character istics, a newfield has been explored, na'mely, th'e synthesisof lubricants fromvarious materials: The products so obtained have been aptly described inthe art as synthetic lubricants.

While many of the synthetic lubricants recently prepared have been founddesirable for various uses in view of a superior characteristic such asimproved oiliness, viscosity, resistance to oxidation, etc., theyinvariably have extremely high pour points which naturally militateagainst their wide use in the art. Generally they suffer too from thedisadvantage of a failure to respond to pour point depressants when thelatter are incor-'-" porated therewith in relatively small amounts.

The present invention is predicated upon the discovery of a method forthe preparation 10f a 3 new and novel class of syntheticlubricants whichare characterized by relatively low pourpoints and which are responsiveto substantial'pour point depression upon the addition of 'small amwms apoint depressant a d arafiin" 40' wax thereto. v v 7 I This is ananomalous discovery inasmuch as parafiin wax has always been removed,not'add'ed,

to a lubricant in order to improve-its pour-=char-"-} acteri'stics;nonetheless, the results provided or more. As appreciated by-thosefamiliar w'ith" the art, the A. S. T. M. pour-testis "accurateto n1yabut5.F Not only arethe new andnovel synthetic-lubfl abovebutthey arefurther characterized by outstanding viscosity index values andoxidation properties,

"'Theimethod contemplated herein for the preparationl of the new andnovel synthetic lubricants involves jreacting certain partiallyhalogenated parafiln' waxes with certain aromatic compounds in thepresence of a Friedel-Crafts catalyst at a condensation temperature andthereafter separatingjthe catalyst and any unchanged reactants from thereactionproducts so obtained. While the present method may be brieflysummarized by the foregoing statement, it is much more complex than asso stated, inasmuch as several of the factors recited therein arecritical in nature and must befollowed religiously lest products of asomewhat inferior character be formed. Specifically, the severalcritical factors, all of which are interrel'ated, include the following:1...: Ype-of paraflin wax,

2. Degreeof halogenation of the paraffin wax,

Aromatic hydrocarbon, andv 4. Proportions of halogenated parafiin waxand of aromatic hydrocarbon.

' 0f importance in the present method is the type of paraflin wax used.We have found that when a-c-rystalline paraffin wax having a meltingpoint not greater than about 140 F. is used, synthetic lubricants ofrelatively low pour point and susceptible'to pour-point depression areobtained. Par-ticularlypreferredwaxes of this type, however, are-thosehaving melting points from about 4 F to about F. These waxes have acrystalline structure, as opposed to other paraflin waxes which do nothave a well-defined crystal structure and are amorphous in character.The latter are connnonly referred to as amorphous waxes, andareconsidered to be undesirable for the; purposes fof this-invention,for such waxes would result in products having relatively highmeltingpoints-and having comparatively little susceptibility to pourpoint depression. Of the waxes-used herein we have found thatparticularly outstanding results are obtained with a crystalline'paraflin wax containing on the average of 24 carbon atoms and having amelting point of about 126"1. It is to be understood, however, that'allcrystalline paraflin waxes characterized by melting points notgreater than about F., and-obtained from all sources, such as petroleumwax fractions, the Fischer-Tropsch synthesis, etc-.-,--'a'recontemplated herein.

' Accordinglmwhen used hereinafter the expression wax," unless otherwisequalified, denotes the desired I reactant: crystalline parafiin wax.This term will also apply to the wax added to the synthetic} lubricantprepared as described herein, together with a pour depressant similarlyadded.

oants of this invention characterized as indicated 66 With" regard tothe degree of halogenation of than onemole of aromatic-hydrocarbon foreach,

wax which must be jollowed, itmay iirst be said. the argmatic reactant,the preferred reaction that all halogens jmaybe used; v-i w: tm atune isabout 80 C., the boil ng point of relative cost, availability,etc.,howvf, chlorine bfi'iene. Similarly, when toluene and xylenes areis preferred and, for these reasons, the following used, the temperaturemay range from 25 C. to description will be confined to the chlorinated5 I98? C and from 25 C. to 145 C., respectively, waxes. In addition,inasmuch as the degi of while thepreferred temperatures are 105 C. andhalogenation of wax is closely allied ,wi h the. about 13;};145? Q,respectively. aromatic hydrocarbon used 'f "th j ffi'llh eagm 'nt 0?catalyst used in the condensatwo factors will be describeditogethermember A 1 tign ;b e relatively small, that is, a catalytic zene is usedas the aromatiehydrocalibqn.mast; ,leplamounti Generally, amounts fromabout 1.0 per ant, the chlorinated wax with which it is reacted cent tgaboutloper cent by weight of the chloroshould contain from 19 to 21.5percent clildf reactant are satisfactory, and amounts of Similarly, withtoluene, the chlorinatedwax th'eorder of 3 per cent are preferred.Catalysts should contain from 12 to 26 per cent chlorineand, suclras:aluminum chloride, zinc chloride, ferric with a xylene, or a mixture ofxylenes, the chlori- 15 chloride, boron trifluoride, hydrogen fluoride,etc., nated wax should contain fromlz to 27. per cent serve-thepurposeso f; this invention; and for this chlorine, Whenchlorineconceiltratibfis iiie re nfthe',catalysts are defined broadlyherein of themaxima recited above are presentin the; as hose capable of,effecting a Friedel-Crafts chlorinated wax reactant, theproductsfobtaizied' type cc de at on, Particularly preferred,howtherewith are'characterizedby .anl'undfiSi fbly, 29 as, chloride.high viscosity, as well. as "little drnoj respo'n" :0, Jmo e-fullyillustrate the method by small, amounts ofa pour point 'depr'es'sa 11dsynthetic lubricants are obtained the wax,In'thesameregard,'when'chlorinated waxes" typical procedure is detailedhereincontaining less 'chlo'rine'th'a'ii the minimarelci fa; 1 above areused, the products so obtain'd'coiitainl f v excwsiveamounts.ofwagandjremarkgd byrleimt x. Example Preparatzon of wax benzene(1 19) or no response to small "amounts or thejaroresi d}addedmaterialsi f It should be understood that, a "12 perv c, htchlorinated wax is onepreparedbyintroduc chlorine into a crystalline'para'fiin wa as defln above; until the weight of thefwaxfhas incl, seabout 12 per cent. 3 Obviously, .tha,'i tne prbeaetj is predominantly aienbgcmo mateawax eon-g taining substantial quantities of'unclilorinatedand polychlorinated wax. Correspondingly,a- 20 per cent chlorinated-waxis predominately-(ii chlorinated wax with substantialquantitiesofunchlorinated wax, monoechloro wax and: more highlychlorinated wax. I H 1e, h w

It will be clear from the. foregoing-thatthe then; yriifle byfilteringthrough acontactclay a m d es i n ieiiis.eentem isi si: a' i mere miiiim. e l h filtrate is herein are benzene, tfolueneand xylenes It will.theneated remove excess benzene and the also beunderst odQof" coursethat: when gtl e L thereby is a wax-substituted halogens are used inplaceIoi chlorine in-thejali; 4,5,, 3 ng sorne unreacted wax, about 10phatic wax reactangthe ioregoingpercentages W nreactedwax. The unreactedwax is n u y i e su if et e aiiee n propor on; 1.8}310 i, vacuudistillation (it may also be to h let iemie, i hts.- oi;he..i.ndirid1ial. rem d y; epiiven ional ew xins p oee h n The iireslueiei en e e r of itar peda r he. r latire; 5Q s r s en -1 indicating m P PT P I i JS ,eifl heie etai ts, n me y, J 1 PtitQQW h 1 w ro p and hl iee wex n aiemat eh d ocarbona Inlorowa isedin ther e r eerdereto bta n-te es rei eduetsat leashes-e, i .n rr ntf hl i are used herele i i eef.the; iis e's :i romatiehvd coea ma ie t9 9 Ql'iif 'eech-Rmduct illu t ofl helnres nt nreiiticiii sw s relatedpreducis wax which contains oneatomicweight oi; e I which do not possess the superior characteristicse; n s t a ,1e i me1eefan.aromatic; ie ialuh iea ts.nr nar das outl dabovefd qe e i a efi ed-. boven s ed. er--eacbs. h,Zi l1b,, ,QQZ 9Qi f.o r e t n 1- atomic weight of chlprine in the chlorinated-waxreggtgdgbdllZQl-kb iorexainple, can be used again reactant.Accordinglmitwill be clear that the; 60-- igzihqlpigpayeliionotadditionalp d dtha reaction products obtained with such proportionsare predominantly monowax aromaticsfllf less;v

atomic h e ie ine i i ehle tewais s sesll; 391-1 2 413:z s cl llpdllfree of unrea ted wax products of less desirable characterare-obtained.?5 (removed by vacuum distillation, solvent dewax- The letter odu ts unik he e ii e im eted. nsisted]- tisahe in er o ha it. s n t herein,Suffer m the r ia hiii o .ifes en i o, sseiiti lsthati..lh iz h nr e d eemell amounts Of e.Ba l i tde ressant-sad. ms seli... eeeardzins m bothwaxee synthetic W and me e e se item. e e ivelrehiia ulli i d iall snthet c. ubrican s. containin pour points. v e V I I 7Q; relatiigelygsnall; mounts of unreacted wax are The ieesiieri tempera ur s;useiiil-i ihe r ss. entennialedan... .iiii meihed e t ese er iel r ieie iteci tamiii; aniea mi lust ate he u e ior. ch ra art as Friedel-Craftscondensationtemperatures tics of the synthetic lubricants of the presentin, Wh l emperatur f om impasse, q-fil st g al-serene; yp ca exa le e.presented 0 ms' fl' e.u eesaii aoio iiv w iesib szeaei is; hereial eimn; ra ist e he v, t.

210 F., viscosity index and A. S. T. M. pour test of the above syntheticlubricants are shown; all of these characteristics and methods fordetermining the same are well known and need not be further described atthis point. In addition the response of these synthetic lubricants withand without a pour point depressant and added wax is also demonstrated.Also present in Table I for comparison with the synthetic lubricantscontemplated herein are several typical products which are much lessdesirable for use as lubricants. for one reason or another. Forconvenience in identifying the latter products, they are preceded by'an3: in Table I.

wax-toluenes (1-12) to (1-26) and the waxxylenes (1-12) to (l-2'7). Itappears then that a pour point depressant and added wax cooperate insome manner, as yet undetermined, to substantially lower the pour pointof our synthetic lubricants which by themselves have relatively low, andtherefore, desirable pour points.

It will be further noted from inspection of the results provided inTable I that the wax-benzenes (1-19) to (1-21.5) have viscosities (S. U.V.) and viscosity indexes which make them extremely valuable lubricants.The wax-toluenes (l-12) to (1-26) and the wax-xylenes (1-12) to (1-27)are similarly characterized. These synthetic lubri- Table I ASTM PourTests (F.) With Pour Point Depressants, and With or Without Wax s U vASIM Product 210 v. 1. 2% 2% 2% 2% 5%) V y W B2 W Added Added B Added O3 Added Wax ax Wax Wax z wax-benzene (1-12) 48. 7 120.1 x wax-benzene(115) 60. 3 116. 5 wax-benzene (1-19) 91. 0 121.4 wax-benzene (1 100.0112. 7 wax-benzene (1-21.5) 168. 0 106.7 x wax-benzene (1-24) 296. 7105.0 wax-toluene (112) 47. 5 119.8 Wax-toluene (1-18) 61.1 110.0wax-toluene (126) 128.2 71.1 a: wax-toluene (l-28) 187.0 69. 5wax-xylene (l-12) 44. 4 119.0 wax-xylene (1-21)... 63. 6 89. 5wax-xylene (1-27) 124. 0 49. 7 z wax-xylene (l-28) 127. 2 47. 3

1 Pour Depressant A=Tetra-wax phenol phthalate. 2 Pour DepressantB=Wax-naphtha1ene.

3 Pour Depressant O=Stannous phenatestannous carboxylate of wax phenolcarboxylic acid disulfide.

It will be clear on inspection of the pour test results set forth inTable I above that wax-benzenes prepared from a chlorowax containing 12,15 or 1 24 per cent chlorine are erratic in their response to a pourpoint depressant and are similarly responsive to the combination of apour point depressant and added wax. None of these products consistentlyshows a pour point lowering of at least 10 F. when the aforesaidadditives are incorporated therewith in small amounts, and some evenhave higher pour points when the said additives are incorporatedtherewith. Surprisingly,

cants are useful both as automotive and aviation lubricants.

To illustrate the critical nature of the proportions of aromatichydrocarbon and of the halogen wax reactants in obtaining the syntheticlubricants of this invention, and those related materials of somewhatinferior character, several typical examples of wax-toluenes are shownin Table 11 below. The data in this table are similar to.those shown inTable I above and the products not contemplated herein are againidentified by the letter as which precedes them, as a: waxhowever, whenthe chlorowax reactant contains toluene (3-12).

Table II ASTM Pour Tests (F.) With Pour Point Depressants, and With orWithout Wax s. U.V. ggy Product 210 V. I. T t 56% 0%) +2 7 2 7 3/ 7 2 2A Added Added B 2 Added C 3 Added Wax Wax ax Wax wax-toluene (1-12) 47.5 119. 8 +25 +15 +15 wax-toluene (118) 61.1 110.0 +25 5 -5 +5 0 +15 0 +50 wax-toluene (l-26)- 128.2 71.1 +35 +10 +10 +10 I wax-toluene (3-12 42.6 +25 +25 +25 +25 +20 +25 +25 .tWax-tolucne (3-18). 64.9 119. 6 +25 +25+20 +20 +20 +25 +30 a: wax-toluene (3-24). 170. 5 107.4 +15 +20 +10 +20+10 x wax-toluene (512) 42. 6, 141 +20 +20 +25 +25 +20 +25 +30 IWax-toluene (5-18) 83. 3 122. 5 +25 +30 +30 +30 +25 +30 +30 zwax-toluene (5-24) 342. 4 114. 1 +20 +25 +20 +25 +30 1 Pour DcpressantA: Tetra-wax phenol phthalate.

1 Pour Depressant B=Wax-naphthalene.

3 Pour Depressant O= Stannous phenate-stannous catboxylate of wax phenolcarboxylic acid disulfide.

from 19 to 21.5 per cent chlorine, the wax-benzenes obtained therefromare susceptible of at least a 10 F. pour point lowering when smallamounts of a pour point depressant and wax are It will be seen that thewax-toluenc s (1-12) to (l-26) in Table II are responsive to substantialpour point lowering with a pour point depressant and added wax. Yet,wax-toluenes prepared with added th re o. Sim y, a rized areth 75chlorowaxescontainingthe same percentages (12,

excuses l8 and26) of chlorine as thosens'ed in 'the preparation of theaforesaid monowax synthetic lubricants, but :prepared with more than oneI mole of toluene for each atomic weightof chlorine in the chlorowax,are 'not so responsive, For exam-ple, wax-toluene (13-12) has an A. S.T. pour point of +25 F., as has the 'combination'of the same synthetic,a :pour :poin-t depressant and added wax. In some-cases,'as withwax-toluene (3-18) and wax toluene (-24),the pour point of the syntheticwith a pour-point depressantand added waxis higher, ratherthan equal-toor lowe'r than, the pour. point of the synthetic alone.

In. Iables I and II above several typical pour point depressants wereused to illustrate the broad class. It is to be understood, however,that all such additives are broadly contemplated. Preferred, however,are depressants of the waxphenol-phthalate class and of the metalorganic class which are typified by depressants A and C in the tables.Particularly preferred of such materials are tetra-wax phenol phthalate(A) and stannous phenate, stannous 'carboxylate of wax phenolcarboxylic'acid disulfideiC). Although varying amounts of thesematerials may be used, satisfactory results are obtained withconcentrations of from about A per cent'to about per cent.

The paraffin wax which is added to our synthetic lubricants togetherwith a pour point depressant is a microcrystalline parafiin wax having amelting point not greater thanabout 140 F., that is, of the same type ofwax as that-used in the halogenated wax reactant. While about 0.5 percent is preferredfor use, amounts from about 0.25 per cent to about 1.0per cent may also be used. It will be understood, of course, that theamounts of added wax and of the pour point depressant will be determinedto someextent by the degree or pour point lowering of the :syntheticlubricant required for a; particular use.

We claim:

1. Themethod of preparing" a synthetic lubricantof low pour point and'susceptible of substantial pour point lowering, .from a crystallineparaffin wax having a meltingpoint notlg'reater than about 140 F. and axylene, which comprises: partially halogenating the 'paraliin :wax toform a mixture of halogenated waxandsubstantially unhalogenated wax,said mixture being selected from the group consisting of awmixturecontaining an amount of halogen corresponding to from 12 to 27 percentchlorine; mixing the halogenated wax and unhalogenate'dwax with saidxylene in the proportion. of at least one mol of-xylene to each atom ofhalogen in the-halogenated wax mixture; adding thereto a "catalystcapable of effecting'a Friedel-Crafts type condensation; heating themixture th us obtained at a Friedel Crafts condensation temperatureuntil substantially all of the halogenated wax has reacted with saidxylene; and separating the Friedel-Crafts catalyst, unreacted xylene andun'halogenated wax from the reaction mixture, so ob tained, to obtainsaid synthetic lubricant.

2. The method of preparing a synthetic lubricant of low pour point andsusceptible of substantial pour point lowering, from a crystallineparafiin wax having a melting point not greater than about 140 F. and axylene, which comprises: partially chlorinating the paraffin wax'to forma mixture of chlorinated wax and substantially' unchlorinated waxcontaining from 12 to 2'7 per cent chlorine mixing the chlorinatedwaxand unchlori-nated wax with said xylene in the unchlorinated waxcontaining from 12 to 27 per cent chlorine; mixing said chlorinated waxand prnportionof at leastone mol of xylene to each atomIof -ehlorinein'the chlorinated wax mixture; adding ia-Friedel-Crafts catalystthereto heating thefmixture .thusobtained under refluxing conditi'onstotheirefiuxing temperature of said xylene untiltsubstantiallyiall of thechlorinated wax has reacted :with said xylene; and separating thefiiedehGrafts' catalyst, unreacted xylene and unchlormated wax from thereaction mixture, so obtained, to-obtain said synthetic lubricant.

3. Thezmethodof preparing a synthetic lubrie'ant-"of lowzpourpoint andsusceptible of substantial .pourrpoint lowering, from a crystallineparaifin wax having a melting point not greater thanabout F. and axylene which comprises: partially chlorinating said paraifin wax to forma mixture of chlorinated wax and substantially unchlorinated waxcontaining from 12 to 27 per centchlorine; mixing said chlorinated waxand unchiorinated waxwith a xylene in the proportioniof'at least onemole of xylene to each atom of chlorine in the chlorinated wax mixture;adding anhydrous aluminum chloride catalyst thereto; heating-the mixturethus obtained under refluxing conditions to the refluxing temperature ofsaid xylene until substantially all oi-said chlorinated wax has reactedwith said xylene; and separating "said aluminum chloride, unreactedxylene and unchlorinated wax from the reaction mixture, so obtained, toobtain said synthetic lubricant. V 4. The method of preparing asynthetic lubricarit of low pour point from a crystalline paraflin 'waxhaving a melting point not greater than about'l40 'F. and a xylene,which comprises: partiallyhalogenating the parafiin wax toform a mixtureof halogenated wax and substantially xiii-halogenated wax containing anamount of halogenfcorrespond-ing to from 12to 27 per centchlorinaforrreaction with a xylene; mixing the halogenatedwax andunhalogena-ted wax with said xylene in the proportion of at least onemole of -xylene toeachatom of halogen in the haloge'nat-ed" wax mixture;adding thereto a catalyst capable of-veffecting a Frieda-Crafts typecondensationyheating the'mixture thus obtained at ardiriedel-Crafts'coridensation temperature until substantially allof the halogenated waxhas reacted with lsaid. xylene; separating the Friedel-Crafts-catalyst;-unreacted xylene and unhalogenated wax from thereaction mixture, so obtained; and adding thereto small amounts of apour point depressant and a crystalline paraffin wax having 'a meltingpoint not greater than about 140 F.

5. The method of preparing a synthetic lubricantiof low pour point froma crystalline parafiin wax having a melting point not greater than about140 F. and a xylene, which comprises:

partially chlorinating said paraflin wax to form amixtureof chlorinatedwax and substantially unchlorinated wax with a xylene in the proportionof at least one mole of a xylene to each atom of chlorine in thechlorinated wax mixture; adding anhydrous aluminum chloride catalystthereto; heating the mixture thus obtained under refluxing conditions tothe refluxing temperature of .saidxy1ene until substantially all of saidchlorinated wax has reacted with said xylene; separatin'g said aluminum:chloride, unreacted xylene and unchlorinatedwax from thereactionmixtu-re,=so :obtained and adding. small amounts. of amour-pointdepressantand a crystalline paraiiin wax ofthe typedefined abovethereto.

xylene, by: partially halogenating the parafiin wax to form a mixture ofhalogenated wax and substantially unhalogenated wax containing an amountof halogen corresponding to from 12 to 27 per cent chlorine for reactionwith a xylene; mixing the halogenated wax and unhalogenated wax withsaid xylene in the proportion of at least one mole of xylene to eachatom of halogen in the halogenated wax mixture; adding thereto acatalyst capable of effecting a Friedel-Crafts type condensation;heating the mixture thus obtained at a Friedel-Crafts condensationtemperature until substantially all of the halogenated wax has reactedwith said xylene; and separating the Friedel-Crafts catalyst, unreaotedxylene and unhalogenated wax from the reaction mixture, so obtained, toobtain said synthetic lubricant.

7. A lubricant of low pour point comprising a synthetic lubricant havingincorporated therewith small amounts of a pour point depressant and acrystalline parafiin wax having a melting point not greater than about140 F., said synthetic lubricant being prepared from a crystallineparafiin wax of the type defined above and a xylene by: partiallychlorinating said paraflin wax to form a mixture of chlorinated wax andsubstantially unchlorinated wax, said mixture containing from 12 to 2'7per cent chlorine; mixing the chlorinated wax and unchlorinated wax witha xylene in the proportion of at least one mole of said xylene to eachatom of chlorine in the chlorinated wax mixture; adding anhydrousaluminum chloride catalyst thereto; heating the mixture thus obtainedunder refluxing conditions to the refluxing temperature of said xyleneuntil substantially all of the chlorinated wax has reacted with saidxylene; and separating said aluminum. chloride, unreaoted xylene andunchlorinated wax from the reaction mixture, so obtained, to obtain saidsynthetic lubricant.

8. The method of preparing a synthetic lubricant of low pour point andsusceptible of substantial pour point lowering from a crystallineparafiln wax having a melting point not greater than about 140 F. and axylene, which comprises: partially halogenating the parafiin wax to forma mixture of halogenated wax and substantially unhalogenated wax, saidmixture being selected from the group consisting of a mixture containingan amount of halogen corresponding to from 12 to 27 per cent chlorine;mixing the halogenated wax and unhalogenated wax with said xylene in theproportion of at least one mol of xylene to each atom of halogen in thehalogenated wax mixture; adding thereto a catalyst capable of eifectinga Friedel-Crafts type condensation; heating the mixture thus obtained ata Friedel- Crafts condensation temperature until substantially all ofthe halogenated wax has reacted with said xylene; and separating theFriedel-Crafts catalyst, unreaoted xylene and substantially allunhalogenated wax from the reaction mixture, so obtained, to obtain saidsynthetic lubricant.

9. The method of preparing a synthetic lubricant of low pour point andsusceptible of substantial pour point lowering, from a crystallineparaffin wax having a melting point not greater than about F. and axylene, which comprises: halogenating the parafiin wax to form ahalogenated Wax selected from the group consisting of a halogenated waxcontaining an amount of halogen corresponding to from 12 to 27 per centchlorine; mixing the halogenated wax and said xylene in the proportionof at least one mol of xylene to each atom of halogen in the halogenatedwax; adding thereto a catalyst capable of effecting a Friedel-Craftstype condensation; heating the mixture thus obtained at a Friedel-Craftscondensation temperature until substantially all of the halogenated waxhas reacted with said xylene; and separating the Friedel-Crafts catalystand any unreaoted xylene from the reaction mixture,

so obtained, to obtain said synthetic lubricant.

ORLAND M. REIFF.

HOWARD D. HARTOUGH.

HARRY J. ANDRESS, JR.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 2,339,493 Lieber et a1 Jan. 18,1944 2,297,292 Davis et al Sept. 29, 1943 2,189,924 Pier et a1 Feb. 13,1940 2,048,466 Reiff et a1 July 21, 1936 2,350,571 Schilling June 6,1944 FOREIGN PATENTS Number Country Date 478,972 Great Britain Jan. 2'7,1938 491,522 Great Britain Sept. 5, 1938 OTHER REFERENCES The CondensedChemical Dictionary, third edition, 1942, Reinhold Publishing Co., NewYork. Page 487.

